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DOI | 10.1038/s41467-018-03332-7 |
Enantioselective radical conjugate additions driven by a photoactive intramolecular iminium-ion-based EDA complex | |
Cao, Zhong-Yan1; Ghosh, Tamal1; Melchiorre, Paolo1,2 | |
2018-08-16 | |
发表期刊 | NATURE COMMUNICATIONS
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ISSN | 2041-1723 |
出版年 | 2018 |
卷号 | 9 |
文章类型 | Article |
语种 | 英语 |
国家 | Spain |
英文摘要 | The photochemical activity of electron donor-acceptor (EDA) complexes provides a way to generate radicals under mild conditions. This strategy has found application in chemical synthesis and recently in enantioselective catalysis. Reported methods classically relied on the formation of intermolecular EDA complexes, generated upon aggregation of two suitable reagents. Herein, we further expand the synthetic utility of this strategy demonstrating that an intramolecular EDA complex can trigger a photochemical catalytic enantioselective radical process. This approach enables radical conjugate additions to ss-substituted cyclic enones to form quaternary carbon stereocenters with high stereocontrol using visible light irradiation. Crucial for success is the use of an amine catalyst, adorned with a carbazole moiety, which generates, upon condensation with enones, chiral iminium ions that show a broad absorption band in the visible region. This optical property originates from an intramolecular charge transfer pi-pi interaction between the electron-rich carbazole nucleus and the electron-deficient iminium double bond. |
领域 | 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000441768300005 |
WOS关键词 | DONOR-ACCEPTOR COMPLEX ; LEWIS-ACID CATALYSIS ; VISIBLE-LIGHT ; CHARGE-TRANSFER ; PHOTOREDOX CATALYSIS ; ALPHA-ALKYLATION ; METAL-FREE ; PHOTOCHEMICAL ACTIVITY ; SYNTHETIC APPLICATIONS ; MODERN STRATEGIES |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
URL | 查看原文 |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/203711 |
专题 | 资源环境科学 |
作者单位 | 1.Barcelona Inst Sci & Technol, Inst Chem Res Catalonia, ICIQ, Avinguda Paisos Catalans 16, Tarragona 43007, Spain; 2.Catalan Inst Res & Adv Studies, ICREA, Passeig Lluis Co 23, Barcelona 08010, Spain |
推荐引用方式 GB/T 7714 | Cao, Zhong-Yan,Ghosh, Tamal,Melchiorre, Paolo. Enantioselective radical conjugate additions driven by a photoactive intramolecular iminium-ion-based EDA complex[J]. NATURE COMMUNICATIONS,2018,9. |
APA | Cao, Zhong-Yan,Ghosh, Tamal,&Melchiorre, Paolo.(2018).Enantioselective radical conjugate additions driven by a photoactive intramolecular iminium-ion-based EDA complex.NATURE COMMUNICATIONS,9. |
MLA | Cao, Zhong-Yan,et al."Enantioselective radical conjugate additions driven by a photoactive intramolecular iminium-ion-based EDA complex".NATURE COMMUNICATIONS 9(2018). |
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